Issue 20, 2020
From the journal:

Organic Chemistry Frontiers

Rhodium(iii)-catalyzed carboxylate-directed ortho-selective thiolation of benzoic acids†

Dongjie Wang,‡a   Kehan Zhou,‡a   Jingyu Zhang*b  and  Yingsheng Zhao ORCID logo *a  

* Corresponding authors

a Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China
E-mail: yszhao@suda.edu.cn

b College of Energy, Soochow Institute for Energy and Materials Innovations, Soochow University, Suzhou 215006, China
E-mail: jyzhang@suda.edu.cn

Abstract

A regioselective rhodium-catalyzed carboxylate-directed thiolation process was developed. Several benzoic-acid derivatives and disulfides were found to be well-tolerated, and they yielded the corresponding products in moderate to good yields. Compounds such as the key precursor of roflumilast can be obtained via this reaction, thereby highlighting the potential of this synthetic approach.

Graphical abstract: Rhodium(iii)-catalyzed carboxylate-directed ortho-selective thiolation of benzoic acids

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Article information

DOI
https://doi.org/10.1039/D0QO00940G
Article type
Research Article
Submitted
07 Aug 2020
Accepted
12 Sep 2020
First published
18 Sep 2020

Org. Chem. Front., 2020,7, 3229-3233

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Rhodium(III)-catalyzed carboxylate-directed ortho-selective thiolation of benzoic acids

D. Wang, K. Zhou, J. Zhang and Y. Zhao, Org. Chem. Front., 2020, 7, 3229 DOI: 10.1039/D0QO00940G

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